Cannot connect Office 365 email with Outlook 2010 Getting error as "Trying to connect" or Outlook 2010 asking for password again and again

If you are unable to connect to Office 365 email with Outlook 2010 Getting error as "Trying to connect" or Outlook 2010 asking for password again and again

The resolution to this issue is simple Please follow the below to the letter and I guarantee it will work.

Install Microsoft Office 2010 SP2. Make sure you have followed this step as its very important. SP2 contains bug fixes regarding the subject issue.

Restart if required,

now remove all email profiles on the machine via the mail (32bit) utility

Create a new mail profile and open Outlook

When the wizard loads choose to configure a new exchange account

For the server enter: outlook.office365.com

Email and password should be the Office 365 email and password

Click "More Settings" in the bottom right

Under the Advanced tab uncheck "Download shared folders".

Under the security tab, in the "Logon network security" drop-down select Anonymous Authentication.

Under the 'connection' tab check "Connect to Microsoft Exchange using HTTP".

Click "Exchange Proxy Settings" use the URL: outlook.office365.com

Tick "Only connect to proxy servers that have this principal name in their certificate" and enter: msstd:outlook.com (Please be aware that there's a typo in the screenshot below; the description here is correct.)

Check both the checkboxes

Under "proxy authentication settings" drop down select "Basic Authentication".

Now reload Outlook and sign in at the first prompt. Be sure to check "Remember password".

It will work surely without any issue.